Im actually quite excited about this. Not that this will help in anyway, but id put my money on you. The odds are very much against you, but Judo is just as much about adaptability as any other martial art. Im looking to start Judo next week at a relatively reputable club. I have an awkward frame, and im not really getting enough time to work on my throws in JJ.

Boxing Gloves and No Gi is ambitious as hell. Im coming just to see this.
Also, are the rules decided by the competitors? i.e san shou rules, MMA.

San Shou rules. Static clinches are broken in 3 seconds. Clinches with movement over in 5. We restart in the middle if one of us sets foot outside the area. If he puts his hand or knee on the floor during the takedown, or otherwise goes down with me, it doesn't count.

I intend on deliberately clinching with him to try and throw him. Why? Because 2 minutes of running around the mat diving in for an occasional brief punch combo to game the rules about 'showing sufficient aggression' is bullshit, that's why.

I will wrestle and play Judo with him afterwards, but I'm not betting on those.

San Shou rules. Static clinches are broken in 3 seconds. Clinches with movement over in 5. We restart in the middle if one of us sets foot in the area. If he puts his hand or knee on the floor during the takedown, or goes down with me, it doesn't count.

Really? That rulebook you linked me to says that you can throw and go down with them, or at least I interpreted it that way.

Article 21 - Scoring Criteria
A competitor will win one point when

21.2.3 both competitors fall down, while he or she remains on top of the opponent,